Donor-acceptor-stabilised germanium analogues of acid chloride, ester, and acyl pyrrole compounds: synthesis and reactivity.

ABSTRACT: Germaacid chloride, germaester, and N-germaacyl pyrrole compounds were not known previously. Therefore, donor-acceptor-stabilised germaacid chloride (i-Bu)₂ATIGe(O)(Cl) ? B(C₆F₅)₃ (1), germaester (i-Bu)₂ATIGe(O)(OSiPh₃) ? B(C₆F₅)₃ (2), and N-germaacyl pyrrole (i-Bu)₂ATIGe(O)(NC₄H₄) ? B(C₆F₅)₃ (3) compounds, with Cl-Ge[double bond, length as m-dash]O, Ph₃SiO-Ge[double bond, length as m-dash]O, and C₄H₄N-Ge[double bond, length as m-dash]O moieties, respectively, are reported here. Germaacid chloride 1 reacts with PhCCLi, KOt-Bu, and RLi (R = Ph, Me) to afford donor-acceptor-stabilised germaynone (i-Bu)₂ATIGe(O)(CCPh) ? B(C₆F₅)₃ (4), germaester (i-Bu)₂ATIGe(O)(Ot-Bu) ? B(C₆F₅)₃ (5), and germanone (i-Bu)₂ATIGe(O)(R) ? B(C₆F₅)₃ (R = Ph 6, Me 7) compounds, respectively. Interconversion between a germaester and a germaacid chloride is achieved; reaction of germaesters 2 and 5 with TMSCl gave germaacid chloride 1, and 1 reacted with Ph₃SiOLi and KOt-Bu to produce germaesters 2 and 5. Reaction of N-germaacyl pyrrole 3 with thiophenol produced a donor-acceptor-stabilised germaacyl thioester (i-Bu)₂ATIGe(O)(SPh) ? B(C₆F₅)₃ (10). Furthermore, the attempted syntheses of germaamides and germacarboxylic acids are also discussed.

SUBMITTER: Sharma MK 

PROVIDER: S-EPMC6472437 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature